SR1664
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522455

CAS#: 1338259-05-4

Description: SR1664 is a potent and selective PPARγ inhibitor with potential antidiabetic activity. SR1664 binds to PPARγ and potently inhibits Cdk5-mediated PPARγ phosphorylation (IC50 = 80 nM; Ki = 28.67 nM) without exhibiting PPARγ agonist activity.

Chemical Structure

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SR1664
CAS# 1338259-05-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 522455
Name: SR1664
CAS#: 1338259-05-4
Chemical Formula: C33H29N3O5
Exact Mass: 547.21
Molecular Weight: 547.610
Elemental Analysis: C, 72.38; H, 5.34; N, 7.67; O, 14.61

Price and Availability

Size Price Availability Quantity
25mg USD 250 2 Weeks
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1250 2 Weeks
500mg USD 2650 2 Weeks
1g USD 3850 2 Weeks
2g USD 6450 2 Weeks
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Synonym: SR1664; SR-1664; SR 1664.

IUPAC/Chemical Name: (S)-4'-((2,3-dimethyl-5-((1-(4-nitrophenyl)ethyl)carbamoyl)-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid

InChi Key: IIJDFXNUWZTHIM-NRFANRHFSA-N

InChi Code: InChI=1S/C33H29N3O5/c1-20-22(3)35(19-23-8-10-25(11-9-23)28-6-4-5-7-29(28)33(38)39)31-17-14-26(18-30(20)31)32(37)34-21(2)24-12-15-27(16-13-24)36(40)41/h4-18,21H,19H2,1-3H3,(H,34,37)(H,38,39)/t21-/m0/s1

SMILES Code: O=C(C1=CC=CC=C1C2=CC=C(CN3C(C)=C(C)C4=C3C=CC(C(N[C@H](C5=CC=C([N+]([O-])=O)C=C5)C)=O)=C4)C=C2)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, DMF, and ethanol

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: SR1664 blocks PPARγ)by cyclin-dependent kinase 5 with an IC50 value of 80 nM (Ki = 28.7 nM) without exhibiting agonist activity at the PPARγ receptor.
In vitro activity: To be determined
In vivo activity: SR1664 improved mice insulin sensitivity and reduced fibrosis in the high fat and high carbohydrate (HFHC) diet, suggesting selective PPARγ modulation is effective in obesity-related liver fibrosis. SR1664 did not alter weight gain, fasting insulin, or glucose levels. The degree of fibrosis was significantly reduced by SR1664 in mice on the HFHC diet, and this was accompanied by a decrease in activated hepatic stellate cells. Reference: Biology (Basel). 2023 Sep 26;12(10):1287. https://pubmed.ncbi.nlm.nih.gov/37886997/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 36.52
DMSO 15.0 27.39
Ethanol 15.0 27.39

Preparing Stock Solutions

The following data is based on the product molecular weight 547.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. McVicker BL, Simpson RL, Hamel FG, Bennett RG. Reduction in Obesity-Related Hepatic Fibrosis by SR1664. Biology (Basel). 2023 Sep 26;12(10):1287. doi: 10.3390/biology12101287. PMID: 37886997; PMCID: PMC10604321. 2. McVicker BL, Hamel FG, Simpson RL, Bennett RG. A Selective PPARγ Modulator Reduces Hepatic Fibrosis. Biology (Basel). 2020 Jul 2;9(7):151. doi: 10.3390/biology9070151. PMID: 32630819; PMCID: P
In vitro protocol: To be determined
In vivo protocol: 1. McVicker BL, Simpson RL, Hamel FG, Bennett RG. Reduction in Obesity-Related Hepatic Fibrosis by SR1664. Biology (Basel). 2023 Sep 26;12(10):1287. doi: 10.3390/biology12101287. PMID: 37886997; PMCID: PMC10604321. 2. McVicker BL, Hamel FG, Simpson RL, Bennett RG. A Selective PPARγ Modulator Reduces Hepatic Fibrosis. Biology (Basel). 2020 Jul 2;9(7):151. doi: 10.3390/biology9070151. PMID: 32630819; PMCID: P

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1: Asteian A, Blayo AL, He Y, Koenig M, Shin Y, Kuruvilla DS, Corzo CA, Cameron MD, Lin L, Ruiz C, Khan S, Kumar N, Busby S, Marciano DP, Garcia-Ordonez RD, Griffin PR, Kamenecka TM. Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists. ACS Med Chem Lett. 2015 Aug 4;6(9):998-1003. doi: 10.1021/acsmedchemlett.5b00218. eCollection 2015 Sep 10. PubMed PMID: 26396687; PubMed Central PMCID: PMC4569877.

2: Milton FA, Cvoro A, Amato AA, Sieglaff DH, Filgueira CS, Arumanayagam AS, de Lima Mdo C, Pitta IR, de Assis Rocha Neves F, Webb P. PPARγ partial agonist GQ-16 strongly represses a subset of genes in 3T3-L1 adipocytes. Biochem Biophys Res Commun. 2015 Aug 28;464(3):718-23. doi: 10.1016/j.bbrc.2015.07.011. Epub 2015 Jul 10. PubMed PMID: 26168725.

3: Marciano DP, Kuruvilla DS, Boregowda SV, Asteian A, Hughes TS, Garcia-Ordonez R, Corzo CA, Khan TM, Novick SJ, Park H, Kojetin DJ, Phinney DG, Bruning JB, Kamenecka TM, Griffin PR. Pharmacological repression of PPARγ promotes osteogenesis. Nat Commun. 2015 Jun 12;6:7443. doi: 10.1038/ncomms8443. PubMed PMID: 26068133; PubMed Central PMCID: PMC4471882.

4: Choi JS, Choi SS, Kim ES, Seo YK, Seo JK, Kim EK, Suh PG, Choi JH. Flightless-1, a novel transcriptional modulator of PPARγ through competing with RXRα. Cell Signal. 2015 Mar;27(3):614-20. doi: 10.1016/j.cellsig.2014.11.035. Epub 2014 Dec 2. PubMed PMID: 25479590.

5: Choi SS, Kim ES, Koh M, Lee SJ, Lim D, Yang YR, Jang HJ, Seo KA, Min SH, Lee IH, Park SB, Suh PG, Choi JH. A novel non-agonist peroxisome proliferator-activated receptor γ (PPARγ) ligand UHC1 blocks PPARγ phosphorylation by cyclin-dependent kinase 5 (CDK5) and improves insulin sensitivity. J Biol Chem. 2014 Sep 19;289(38):26618-29. doi: 10.1074/jbc.M114.566794. Epub 2014 Aug 6. PubMed PMID: 25100724; PubMed Central PMCID: PMC4176243.

6: Norris AW, Sigmund CD. A second chance for a PPARγ targeted therapy? Circ Res. 2012 Jan 6;110(1):8-11. doi: 10.1161/RES.0b013e3182435d88. PubMed PMID: 22223206; PubMed Central PMCID: PMC3583552.

7: Choi JH, Banks AS, Kamenecka TM, Busby SA, Chalmers MJ, Kumar N, Kuruvilla DS, Shin Y, He Y, Bruning JB, Marciano DP, Cameron MD, Laznik D, Jurczak MJ, Schürer SC, Vidović D, Shulman GI, Spiegelman BM, Griffin PR. Antidiabetic actions of a non-agonist PPARγ ligand blocking Cdk5-mediated phosphorylation. Nature. 2011 Sep 4;477(7365):477-81. doi: 10.1038/nature10383. PubMed PMID: 21892191; PubMed Central PMCID: PMC3179551.